2-aminoethyl 5-acetamido-9-(2-chlorobenzoylamino)-3,5,9-trideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonate-(2-6)-O-β-D-galactopyranosyl-(1-4)-O-2-acetamido-2-deoxy-β-D-glucopyranoside | 1030361-22-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-aminoethyl 5-acetamido-9-(2-chlorobenzoylamino)-3,5,9-trideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonate-(2-6)-O-β-D-galactopyranosyl-(1-4)-O-2-acetamido-2-deoxy-β-D-glucopyranoside
• 英文别名: Bz(2-Cl)NH(-9d)NeuAc(a2-6)Gal(b1-4)GlcNAc(b)-O-EtNH2；(2R,4S,5R,6R)-5-acetamido-2-[[(2R,3R,4S,5R,6S)-6-[(2R,3S,4R,5R,6R)-5-acetamido-6-(2-aminoethoxy)-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-[(1R,2R)-3-[(2-chlorobenzoyl)amino]-1,2-dihydroxypropyl]-4-hydroxyoxane-2-carboxylic acid
• CAS: 1030361-22-8
• 化学式: C₃₄H₅₁ClN₄O₁₉
• 分子量: 855.247
• InChiKey: XEDXNQYDTSVYNQ-SCMWPTIHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.2
• 重原子数：
  58
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  368
• 氢给体数：
  13
• 氢受体数：
  20

反应信息

• 作为产物：
  描述：

  在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 48.0h， 生成 2-aminoethyl 5-acetamido-9-(2-chlorobenzoylamino)-3,5,9-trideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonate-(2-6)-O-β-D-galactopyranosyl-(1-4)-O-2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Sialoside Analogue Arrays for Rapid Identification of High Affinity Siglec Ligands

  摘要：

  The siglec family of sialic acid binding proteins participates in diverse I cell surface biology that includes regulation of immune cell signaling and the interaction of neuronal cells with glial cells. The weak intrinsic affinity of the natural sialoside ligands has hampered the development of synthetic ligand based probes needed to elucidate their roles in siglec function. In this report, we describe a glycan microarray comprising a library of 9-acyl-substituted sialic acids incorporated into sialosides containing the Neu5Aca2-3Gal and Neu5Aca2-6Gal linkages commonly recognized by the siglecs. The array is demonstrated to exhibit utility for detecting 9-acyl substituents that increase the affinity of siglecs for their ligands. Substituents that increase affinity are anticipated to be useful for the design of high affinity ligand based probes of siglec function.

  DOI：

  10.1021/ja801052g

文献信息

• Sialoside Analogue Arrays for Rapid Identification of High Affinity Siglec Ligands
  作者：Ola Blixt、Shoufa Han、Liang Liao、Ying Zeng、Julia Hoffmann、Satoshi Futakawa、James C. Paulson

  DOI：10.1021/ja801052g

  日期：2008.5.1

  The siglec family of sialic acid binding proteins participates in diverse I cell surface biology that includes regulation of immune cell signaling and the interaction of neuronal cells with glial cells. The weak intrinsic affinity of the natural sialoside ligands has hampered the development of synthetic ligand based probes needed to elucidate their roles in siglec function. In this report, we describe a glycan microarray comprising a library of 9-acyl-substituted sialic acids incorporated into sialosides containing the Neu5Aca2-3Gal and Neu5Aca2-6Gal linkages commonly recognized by the siglecs. The array is demonstrated to exhibit utility for detecting 9-acyl substituents that increase the affinity of siglecs for their ligands. Substituents that increase affinity are anticipated to be useful for the design of high affinity ligand based probes of siglec function.